WO2020203958A1 - ポリカーボネート樹脂 - Google Patents

ポリカーボネート樹脂 Download PDF

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Publication number
WO2020203958A1
WO2020203958A1 PCT/JP2020/014513 JP2020014513W WO2020203958A1 WO 2020203958 A1 WO2020203958 A1 WO 2020203958A1 JP 2020014513 W JP2020014513 W JP 2020014513W WO 2020203958 A1 WO2020203958 A1 WO 2020203958A1
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Prior art keywords
carbon atoms
substituent
group
polycarbonate resin
bisphenol
Prior art date
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PCT/JP2020/014513
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English (en)
French (fr)
Japanese (ja)
Inventor
駿 石川
小川　典慶
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三菱瓦斯化学株式会社
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Application filed by 三菱瓦斯化学株式会社 filed Critical 三菱瓦斯化学株式会社
Priority to CN202080025018.0A priority Critical patent/CN113646359B/zh
Priority to US17/598,531 priority patent/US12006398B2/en
Priority to KR1020217022235A priority patent/KR20210146282A/ko
Priority to EP20784776.5A priority patent/EP3950771A4/en
Priority to JP2021512107A priority patent/JPWO2020203958A1/ja
Publication of WO2020203958A1 publication Critical patent/WO2020203958A1/ja

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/045—Aromatic polycarbonates containing aliphatic unsaturation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/04—Aromatic polycarbonates
    • C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
    • C08G64/08—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen
    • C08G64/12—Aromatic polycarbonates not containing aliphatic unsaturation containing atoms other than carbon, hydrogen or oxygen containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/20—General preparatory processes
    • C08G64/22—General preparatory processes using carbonyl halides
    • C08G64/24—General preparatory processes using carbonyl halides and phenols
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
    • C08G64/42—Chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule

Definitions

  • the present invention relates to a novel terminal-modified polycarbonate resin.
  • polycarbonate having terminal reaction activity examples include polycarbonate having a vinyl terminal and a conjugated double bond (Patent Documents 1 and 2). Although they have ultraviolet absorbency, they have high reaction activity, so that they react with ultraviolet rays outdoors and polymerize, and have the disadvantage that they lose their activity and also lose their function as ultraviolet absorbers. Further, a polycarbonate having a triazole or benzophenone type ultraviolet absorber at the terminal is known (Patent Document 3). However, although these UV absorbers show excellent weather resistance, they have low activity as reactive groups and are not suitable for use as raw materials for manufacturing block copolymers with other resins or as reactive resin modifiers. It was.
  • terminal-modified polycarbonate resins include terminal-modified polycarbonate oligomers whose ends are terminated with a chalcone derivative (Patent Document 4) and polycarbonate resins having a terminal group having a specific structure having a benzotriazole ring (Patent Document 5).
  • Patent Document 4 terminal-modified polycarbonate oligomers whose ends are terminated with a chalcone derivative
  • Patent Document 5 polycarbonate resins having a terminal group having a specific structure having a benzotriazole ring
  • the present invention includes the following embodiments.
  • R 1 is hydrogen or an alkyl group having 1 to 6 carbon atoms
  • R 2 is an alkylene group having 1 to 6 carbon atoms
  • R 3 is a hydrogen or methyl group
  • R 4 is hydrogen or a halogen. Represented, * represents the bonding position with the main chain of the polycarbonate resin.
  • R 5 to R 8 are independently hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an alkoxy having 1 to 5 carbon atoms which may have a substituent.
  • R 9 and R 10 may independently have a hydrogen, a halogen, and an alkyl group having 1 to 20 carbon atoms and a substituent. It has a good alkoxy group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or a substituent.
  • It represents an alkenyl group having 2 to 15 carbon atoms which may be used, or R 9 and R 10 combine with each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms; c represents an integer from 0 to 20; R 11 and R 12 are independently hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, and a substituent.
  • R 11 and R 12 combine with each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms;
  • R 13 to R 16 are independently hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, and a substituent.
  • R 13 and R 14 and R 15 and R 16 respectively combine with each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms;
  • R 17 to R 26 each independently represent hydrogen or an alkyl group having 1 to 3 carbon atoms, and at least one of R 17 to R 26 is an alkyl group having 1 to 3 carbon atoms.
  • a novel terminal-modified polycarbonate resin having an excellent ultraviolet absorbing ability can be obtained.
  • the present invention relates to a terminal-modified polycarbonate resin having a structure represented by the general formula (A) and a structural unit derived from divalent phenol:
  • R 1 is hydrogen or an alkyl group having 1 to 6 carbon atoms
  • R 2 is an alkylene group having 1 to 6 carbon atoms
  • R 3 is a hydrogen or methyl group
  • R 4 is hydrogen or halogen. Represented, * represents the bonding position of the polycarbonate resin with the main chain.).
  • the terminal-modified polycarbonate resin of the present invention may be a terminal-modified polycarbonate resin having a structural unit represented by the following general formula (1) and whose terminal group is represented by the general formula (A).
  • R 5 to R 8 are independently hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, and an alkoxy having 1 to 5 carbon atoms which may have a substituent.
  • R 9 and R 10 may independently have a hydrogen, a halogen, and an alkyl group having 1 to 20 carbon atoms and a substituent. It has a good alkoxy group having 1 to 5 carbon atoms, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 17 carbon atoms which may have a substituent, or a substituent.
  • It represents an alkenyl group having 2 to 15 carbon atoms which may be used, or R 9 and R 10 combine with each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms; c represents an integer from 0 to 20; R 11 and R 12 are independently hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, and a substituent.
  • R 11 and R 12 combine with each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms;
  • R 13 to R 16 are independently hydrogen, halogen, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an alkoxy group having 1 to 5 carbon atoms which may have a substituent, and a substituent.
  • R 13 and R 14 and R 15 and R 16 respectively combine with each other to form a carbon ring with 3 to 20 carbon atoms or a heterocycle with 1 to 20 carbon atoms
  • R 17 to R 26 independently represent hydrogen or an alkyl group having 1 to 3 carbon atoms
  • R 1 At least one of 7 ⁇ R 26 is an alkyl group having 1 to 3 carbon atoms.
  • X in the structural unit represented by the general formula (1) may be a divalent group represented by the general formula (3).
  • the divalent phenol may be a bisphenol compound.
  • the bisphenol compound used as the divalent phenol in the present invention include 2,2-bis (4-hydroxy-3,5-dibromophenyl) propane and 2,2-bis (4-hydroxy-3,5-).
  • Dichlorophenyl) propane 2,2-bis (4-hydroxy-3-bromophenyl) propane, 2,2-bis (4-hydroxy-3-chlorophenyl) propane, 2,2-bis (4-hydroxy-3-methyl) Phenyl) propane, 2,2-bis (4-hydroxy-3,5-dimethylphenyl) propane, 1,1-bis (4-hydroxyphenyl) -1-phenylethane, bis (4-hydroxyphenyl) diphenylmethane, ⁇ , ⁇ -bis [3- (O-hydroxyphenyl) propyl] polydimethylsiloxane, 2,2-bis (4-hydroxyphenyl) propane (bisphenol A; BPA), 1,1-bis (4-hydroxyphenyl)- 1-Phenylethane (bisphenol AP), 2,2-bis (4-hydroxyphenyl) butane (bisphenol B; BPB), bis (4-hydroxyphenyl) diphenylmethane (bisphenol BP), bisphenol CD, 2,2-bis ( 3-Methyl-4-hydroxyphenyl) Prop
  • the bisphenol compound can be selected from the group consisting of bisphenol A, bisphenol AP, bisphenol Z, bisphenol CD, bisphenol C, bisphenol IOTD, bisphenol IBTD, and bisphenol MIBK.
  • the divalent phenol may be used alone or in combination of two or more.
  • the monohydric phenol (also referred to as "terminal terminator A"), which is a precursor of the structure represented by the above general formula (A), can be easily obtained from the market as an ultraviolet absorber.
  • the monovalent phenol may be used alone or in combination of two or more.
  • the terminal structure represented by the general formula (A) may be a structure represented by the following formula (7).
  • * represents the bonding position of the polycarbonate resin with the main chain.
  • the terminal structure represented by the general formula (A) may be contained preferably in an amount of 0.5% by mass to 15% by mass with respect to the structural unit derived from the divalent phenol. ..
  • the terminal structure represented by the general formula (A) is more preferably 1% by mass to 10% by mass, still more preferably 2% by mass to 10% by mass, based on the structural unit derived from the divalent phenol. Particularly preferably, it may be contained in an amount of 3% by mass to 7% by mass.
  • the terminal-modified polycarbonate resin may contain any of a random copolymer structure, a block copolymer structure, and an alternate copolymer structure.
  • the terminal-modified polycarbonate resin can be blended with another resin to obtain a terminal-modified polycarbonate resin composition.
  • other resins include, but are not limited to, polyamides, polyacetals, polycarbonates, modified polyphenylene ethers, polyethylene terephthalates, polybutylene terephthalates and the like.
  • the terminal-modified polycarbonate resin can be made into a terminal-modified polycarbonate resin composition by adding an antioxidant and a mold release agent as additives.
  • Antioxidants include triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate] and 1,6-hexanediol-bis [3- (3,5-di).
  • -Tert-Butyl-4-hydroxyphenyl) propionate pentaerythritol-tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate]
  • octadecyl-3- (3,5-di-) tert-Butyl-4-hydroxyphenyl) propionate 1,3,5-trimethyl-2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, N, N-hexamethylene Bis (3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 3,5-di-tert-butyl-4-hydroxy-benzylphosphonate-die
  • the content of the antioxidant is preferably 0.50% by mass or less, more preferably 0.10 to 0.40% by mass, and 0.20 to 0% in the terminal-modified polycarbonate resin composition. It is particularly preferably .40% by mass.
  • the release agent it is preferable that 90% by mass or more thereof is an ester of alcohol and fatty acid.
  • the ester of the alcohol and the fatty acid include an ester of a monohydric alcohol and a fatty acid, a partial ester of a polyhydric alcohol and a fatty acid, or a total ester.
  • the ester of the monohydric alcohol and the fatty acid an ester of a monohydric alcohol having 1 to 20 carbon atoms and a saturated fatty acid having 10 to 30 carbon atoms is preferable.
  • partial ester or total ester of the polyhydric alcohol and the fatty acid a partial ester or the total ester of the polyhydric alcohol having 1 to 25 carbon atoms and the saturated fatty acid having 10 to 30 carbon atoms is preferable.
  • examples of the ester of monohydric alcohol and saturated fatty acid include stearyl stearate, palmityl palmitate, butyl stearate, methyl laurate, and isopropyl palmitate.
  • As partial or total esters of polyhydric alcohol and saturated fatty acid stearic acid monoglyceride, stearic acid monoglyceride, stearic acid diglyceride, stearic acid triglyceride, stearic acid monosorbitate, behenic acid monoglyceride, capric acid monoglyceride, laurate monoglyceride, Dipentaerythritol monostearate, pentaerythritol tetrastearate, pentaerythritol tetrapelargonate, propylene glycol monostearate, biphenylbiphenate, sorbitan monostearate, 2-ethylhexyl stearate, dipentaerythritol
  • the content of the release agent is preferably 0.50% by mass or less, more preferably 0.01 to 0.10% by mass, and 0.03 to 0% in the terminal-modified polycarbonate resin composition. It is particularly preferably 0.05% by mass.
  • a processing stabilizer an ultraviolet absorber, a fluidity modifier, a crystal nucleating agent, a strengthening agent, a dye, an antistatic agent, a brewing agent, etc.
  • An antibacterial agent or the like may be added.
  • the terminal-modified polycarbonate resin can be produced by the same method as the conventional method for producing a polycarbonate resin, except that a terminal terminator is used.
  • a terminal terminator and a tertiary amine or quaternary ammonium are used.
  • a method of adding a polymerization catalyst such as a salt for polymerization, or a method of dissolving a divalent phenolic compound and a terminal terminator in a mixed solution of pyridine or a pyridine and an inert solvent in the pyridine method, and blowing phosgen directly to obtain a polycarbonate oligomer. is there.
  • the terminal terminator may be added at the time of reaction between the divalent phenolic compound and phosgene.
  • the viscosity average molecular weight (Mv) of the terminal-modified polycarbonate resin may be preferably 10,000 to 60,000.
  • the viscosity average molecular weight (Mv) of the terminally modified polycarbonate is more preferably 13,000 to 50,000, even more preferably 15,000 to 40,000, and even more preferably 20,000 to 35,000. It is particularly preferably 25,300 to 33,500.
  • the viscosity average molecular weight (Mv) of the polycarbonate is within the above range, it is possible to prevent the molded product from becoming brittle, prevent the melt viscosity from becoming excessively high, facilitate the removal of the resin after production, and further.
  • the fluidity can be improved and injection molding in a molten state can be facilitated.
  • the terminal-modified polycarbonate resin may have a transmittance of 1% or less at 330 nm.
  • the transmittance of the terminal-modified polycarbonate resin of the present invention at 330 nm can be preferably 0.5% or less, more preferably 0.1 or less.
  • the transmittance at 330 nm is within the above range, it can be put into practical use as a terminal-modified polycarbonate resin having both excellent ultraviolet absorption ability and stability against light.
  • the 330 nm transmittance is based on the following conditions: -Measuring equipment: UV-1280 UV-1280 spectrophotometer manufactured by Shimadzu Corporation -Solvent: dichloromethane-Resin solution concentration: 10 w / w% -Cell: 1 cm quartz cell-In photometric mode, zero point correction at 330 nm was performed with a dichloromethane solvent, and then the transmittance of the resin solution was measured.
  • the IR spectrum was obtained by measuring the measured wavenumber range of 4000 to 650 cm -1 by the film method using FT / IR-400 + manufactured by JASCO Corporation.
  • the film was prepared by dissolving a polycarbonate resin in dichloromethane and using a solution cast film method.
  • a terminally modified polycarbonate resin was prepared according to the method described below, and the viscosity average molecular weight (Mv), 330 nm transmittance, and infrared absorption (IR) spectrum of the obtained resin were analyzed.
  • Mv viscosity average molecular weight
  • IR infrared absorption
  • Example 1 To 600 ml of a 9 w / w% sodium hydroxide aqueous solution and 200 ml of pure water, 100 g of bisphenol A (BPA) manufactured by Nippon Steel Chemical & Materials Co., Ltd. and 0.5 g of hydrosulfite were added and dissolved. To this, 330 ml of dichloromethane was added, and while stirring, 59.7 g of phosgene was blown over 30 minutes while keeping the solution temperature in the range of 15 to 25 ° C.
  • BPA bisphenol A
  • the polymerization solution was separated into an aqueous phase and an organic phase, the organic phase was neutralized with phosphoric acid, and washing with pure water was repeated until the pH of the washing solution became neutral.
  • a polycarbonate resin powder was obtained by evaporating and distilling off an organic solvent from the produced polycarbonate resin solution.
  • Example 2 BPA was synthesized in the same manner as in Example 1 except that 87 g of bisphenol AP manufactured by Honshu Chemical Industry Co., Ltd. and 3.2 g of terminal terminator A were changed.
  • Example 3 BPA was synthesized in the same manner as in Example 1 except that 90 g of bisphenol Z manufactured by Honshu Chemical Industry Co., Ltd. and 3.6 g of terminal terminator A were changed.
  • Example 4 BPA was synthesized in the same manner as in Example 1 except that 130 g of bisphenol cyclododecane (bisphenol CD) manufactured by Honshu Chemical Industry Co., Ltd. and 1.75 g of terminal terminator A were changed.
  • Example 5 It was synthesized in the same manner as in Example 1 except that 61.3 g of bisphenol C manufactured by Honshu Chemical Industry Co., Ltd. was used in addition to 41.2 g of BPA and the terminal terminator A was changed to 4.05 g.
  • Example 6 BPA was synthesized in the same manner as in Example 1 except that bisphenol MIBK manufactured by Honshu Chemical Industry Co., Ltd. was changed to 90 g and the terminal terminator A was changed to 3.58 g.
  • Example 7 BPA was synthesized in the same manner as in Example 1 except that 90 g of bisphenol IOTD manufactured by Honshu Chemical Industry Co., Ltd. and 3.25 g of terminal terminator A were changed.
  • Example 8 BPA was synthesized in the same manner as in Example 1 except that 80 g of bisphenol IBTD manufactured by Honshu Chemical Industry Co., Ltd. and 3.55 g of terminal terminator A were changed.
  • Example 9 BPA was synthesized in the same manner as in Example 1 except that 100 g of Honshu Chemical Industry's bisphenol CD, 19.2 g of Honshu Chemical Industry's bisphenol MIBK, and 4.41 g of the terminal terminator A were changed.
  • Example 10 It was synthesized in the same manner as in Example 9 except that the terminal terminator A was changed to 7.17 g.
  • the terminal-modified polycarbonate resin of the present invention has extremely low transmittance at 330 nm and has excellent ultraviolet absorption ability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
PCT/JP2020/014513 2019-04-02 2020-03-30 ポリカーボネート樹脂 WO2020203958A1 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
CN202080025018.0A CN113646359B (zh) 2019-04-02 2020-03-30 聚碳酸酯树脂
US17/598,531 US12006398B2 (en) 2019-04-02 2020-03-30 Polycarbonate resin
KR1020217022235A KR20210146282A (ko) 2019-04-02 2020-03-30 폴리카보네이트 수지
EP20784776.5A EP3950771A4 (en) 2019-04-02 2020-03-30 POLYCARBONATE RESIN
JP2021512107A JPWO2020203958A1 (ko) 2019-04-02 2020-03-30

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Application Number Priority Date Filing Date Title
JP2019-070650 2019-04-02
JP2019070650 2019-04-02

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JP (1) JPWO2020203958A1 (ko)
KR (1) KR20210146282A (ko)
CN (1) CN113646359B (ko)
WO (1) WO2020203958A1 (ko)

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WO2021079893A1 (ja) * 2019-10-23 2021-04-29 三菱瓦斯化学株式会社 硬化用樹脂組成物、その硬化方法及び成形品

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JPS4999596A (ko) 1973-01-25 1974-09-20
JPS559696A (en) 1978-07-04 1980-01-23 Bayer Ag Polycarbonate having end group with uv light crosslinkable double bond
JPS61141726A (ja) 1984-12-11 1986-06-28 バイエル・アクチエンゲゼルシヤフト 芳香族ポリカーボネートおよびその製造法
JPH06145491A (ja) * 1992-11-02 1994-05-24 Mitsubishi Gas Chem Co Inc ポリカーボネート樹脂組成物
JPH06256493A (ja) 1993-03-02 1994-09-13 Mitsubishi Gas Chem Co Inc 末端変性ポリカーボネートオリゴマー及びその製造法
JPH08253575A (ja) * 1994-12-21 1996-10-01 General Electric Co <Ge> ポリマー安定化用高分子量安定剤化合物
JPH09316187A (ja) 1996-05-29 1997-12-09 Teijin Chem Ltd ポリカーボネート樹脂の改質法
JP2002179902A (ja) * 2000-12-15 2002-06-26 Ipposha Oil Ind Co Ltd 耐光性及び紫外線透過防止性に優れたポリカーボネート樹脂組成物
CN104193979A (zh) * 2014-08-19 2014-12-10 万华化学集团股份有限公司 一种抗紫外线聚碳酸酯树脂及其制备方法

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Title
See also references of EP3950771A4

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021079893A1 (ja) * 2019-10-23 2021-04-29 三菱瓦斯化学株式会社 硬化用樹脂組成物、その硬化方法及び成形品

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